Patent DE-102005008021-A1 (DE)
Title: New spiroketal-substituted cyclic ketoenol compounds used for combating animal parasites, undesired plant growth and/or undesired microorganisms
Inventor: BRETSCHNEIDER THOMAS
IPC: C07D493/10
Filed: 2005-02-22
Abstract: Spiroketal-substituted cyclic ketoenol compounds (I) are new. Spiroketal-substituted cyclic ketoenol compounds of formula (I) are new. W 1> : H, (halo)alkyl, alkenyl, alkynyl, (halo)alkoxy, halo, alkenyloxy or CN; X : halo, (halo)alkyl, alkenyl, alkynyl, (halo)alkoxy, (halo)alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, nitro or CN; Y 1>, Z : H, (halo)alkyl, alkenyl, alkynyl, (halo)alkoxy, halo, nitro, CN or optionally substituted (het)aryl (provided that at least one of W 1> or Z is H when X and Y 1> are CH 3); C+A+B 1> : (halo)alkyl, alkoxy, alkoxyalkyl or optionally substituted phenyl substituted 5-7 membered ketal or (di)thioketal, which is interrupted through a further heteroatom; D : NH or O; Q 1>, Q 2> : H, haloalkyl or alkoxy; G : H, -C(=O)-R 1>, -C(=L)-M-R 2>, -SO 2-R 3>, -P(=L)(R 4>)(R 5>), E or -C(=L)-N(R 6>)(R 7>); E : metal ion or ammonium ion; L, M : O or S; R 1> : alkyl, alkenyl, (poly)alkoxyalkyl, alkylthioalkyl (all optionally substituted with halo or CN), cycloalkyl or heterocyclyl (both optionally substituted with halo, alkyl or alkoxy) or optionally substituted (phenyl)alkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl; R 2> : alkyl, alkenyl or (poly)alkoxyalkyl (all optionally substituted with halo or CN) or optionally substituted cycloalkyl, phenyl or benzyl; R 3>-R 5> : alkyl(thio), alkoxy, (di)alkylamino, alkenylthio or cycloalkylthio (all optionally substituted with halo) or optionally substituted phenyl, benzyl, phenoxy or phenylthio; and either R 6>, R 7> : (cyclo)alkyl, alkenyl, alkoxy, alkoxyalkyl (all optionally substituted with halo or CN), phenyl, benzyl (both optionally substituted) or H; or NR 6>R 7> : optionally substituted ring optionally containing O or S. Independent claims are included for: (1) N-cyclohexyl-2-phenyl-acetamide compounds of formula (II); (2) phenyl-acetic acid cyclohexyl ester compounds of formula (III); (3) 1-phenylacetylamino-cyclohexanecarboxylic acid compounds of formula (XVIII); (4) N-(1-cyano-cyclohexyl)-2-phenyl-acetamide compounds of formula (XXI); (5) 1-amino-cyclohexanecarbonitrile compounds of formula (XX); (6) substituted cyclohexanol compounds of formula (XXII); (7) 1,4-dioxa-spiro[4.5]dec-8-ylamine compounds of formula (XVI') or (XVI''); (8) 8-amino-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde compounds of formula (XIX'); (9) 9-amino-1,5-dioxa-spiro[5.5]undecane-9-carboxylic acid compounds of formula (XIX''); (10) 9,12-dioxa-1,3-diaza-dispiro[4.2.4.2]tetradecane-2,4-dione compounds of formula (XXIII'); (11) 9,13-dioxa-1,3-diaza-dispiro[4.2.5.2]pentadecane-2,4-dione compounds of formula (XXIII''); (12) the preparation of (I); (13) an agent, for combating animal parasites, undesired plant growth and/or undesired microorganisms, comprising (I); (14) a method for combating animal parasites, undesired plant growth and/or undesired microorganisms comprising applying (I) on the parasites, undesired plant and undesired microorganisms and/or their habitats; (15) a method for preparing the agent comprising mixing (I) with diluting agents and/or surface active substances; (16) an agent comprising an active combination comprising (I) and at least one culture plant compatibility improving 59 compounds e.g. 4-dichloracetyl-1-oxa-4-aza-spiro[4.5]-decane, 1-(1-methyl-1-phenyl-ethyl)-3-(4-methyl-phenyl)-urea, piperidin-1-thiocarboxylic acid-S-1-methyl-1-phenyl-ethylester, 2,2-dichloro-N,N-di-2-propenyl-acetamide and 1-(ethoxycarbonyl)-ethyl-3,6-di-chloro-2-methoxybenzoate; (17) a method for combating undesirable plant growth comprising applying the agent on the plant or its surrounding; and (18) a method for combating undesirable plant growth comprising applying (I) and the culture plant compatibility increasing compounds in a temporary nearer sequence on the plants or their surroundings. In formula (XVI'): Q 3> : 1-4C alkyl, 1-3C haloalkyl, 1-4C alkoxy or 1-4C alkoxy-1-4C alkyl; and q : 1-3. In formulae (XVI''), (XIX''), (XXIII''):q = 0-3. In formulae (XIX'), (XXIII'): q : 1-3. [Image] [Image] [Image] [Image] [Image] [Image] ACTIVITY : Antiparasitic; Herbicide; Antibacterial; Antimicrobial. The antiparasitic activity of (I) was tested against Aphis gossypii in cotton wool leaves using Aphis gossypii test. The results showed that the percentage of the parasites killed was greater than or equal to 80% after treating with 12-hydroxy-11-(2,4,6-trimethyl-phenyl)-1,4-dioxa-dispiro[4.2.4.2]tetradec-11-en-10-one (200 ppm). MECHANISM OF ACTION : None given.